Siesta Key Vacation Rentals

Find Weekly, Monthly and Annual Rentals
in Siesta Key and Sarasota FL

Monthly Rentals

Stunning 12th floor Penthouse located directly on Siesta Key Beach with Spectacular Full Gulf Views at Whispering Sands. Beautifully renovated 2 bedroom in Siesta Key Village. Private Beach. 2 month minimum, 55+ community. Sleeps 4

First Time Renting and Everything is NEW! This custom home is being offered for rent for the first time and everything inside is new including all furniture, beds, linens, dishes, TV’s etc. Private courtyard with heated pool. Sleeps 13!

Siesta Key Gulf Front Living at it's Finest! Juust steps from Crescent Beach, you are sure to fall in love with this beautiful, spacious 2 bedroom, 2 bath ground floor unit with all the amenities Gulf & Bay Club has to offer. Private beach, 3 pools,

Luxury 2 bedroom condo at exclusive Tortuga Club located directly on the beach. Private beach, indoor/outdoor pool, tennis, boat dock, gulf views, washer/dryer in unit. Sleeps 6

Bright & Airy 2 bedroom waterfront condo with private beach & stunning water views located on the quieter end of Siesta Key at Fisherman's Haven. Heated pool, bay access, gated, friendly community.

Beautiful 5th floor condo with stunning panoramic Gulf views from the wall of windows spanning the entire width of the unit. Office area w/2 desks. Private beach, bay access, gated community. Sleeps 4

Beautiful 5th floor condo with private beach and stunning water views from every room! Spacious, open-concept 2 bedroom, gourmet kitchen, large lanai. Sleeps 4 w/king beds in both bedrooms.

Spacious 3 Bedroom, 2.5 bath Gulf Front with gorgeous water views and private beach. Updated gourmet kitchen, large screened lanai. Located on the quieter Southern end of Siesta Key. Heated pool & bay access. Sleeps 6

Spacious waterfront condo overlooking Turtle Beach Inlet with private beach and bay access. Relax on the large enclosed lanai while watching boats, kayaks & paddle boarders float by on the bay. Sleeps 4

Weekly Rentals

Gorgeous 3 bedroom, 2 story Siesta Key home with private pool, close to the north bridge for easy access on and off the island. Full size washer & dryer. 2 patio areas. Bicycles, beach toys, and many more extras provided. Sleeps 8.

First Time Renting and Everything is NEW! This custom home is being offered for rent for the first time and everything inside is new including all furniture, beds, linens, dishes, TV’s etc. Private courtyard with heated pool. Sleeps 13!

Stunning views of everything from the Gulf of Mexico & Siesta Key Beach to fantastic sunsets & downtown Sarasota. Located just across from world-famous Siesta Key Beach. Walk to Siesta Key Village by sidewalk or beach. Sleeps 6

Watch the sunset from the wrap around balconies in this beautifully decorated 2 bedroom condo directly across from Siesta Key Beach. Spacious and inviting with ceiling to floor sliders on two entire walls for incredible views. Sleeps 6

Enjoy gorgeous Bay views from the balcony of this beautifully appointed third floor condo located in the heart of Siesta Key! Enjoy private beach access as well as bay access. 2 heated pools, custom hot tub overlooking the Bay, fishing pier, boat doc

2 bedroom condo located on world famous Crescent Beach in Siesta Key! Private beach area with loungers provided. Enjoy the tiki hut BBQ/picnic area on the beach. Nicely furnished and close to dining, shopping, and night time entertainment.

2 bdrm, 2 bath condo with screened lanai located at Bay Oaks resort on Siesta Key. Beautiful bayside waterfront picnic area where dolphins can be seen passing by. 2 large fishing piers w/fish cleaning station. Sleeps 4

Charming 2 bdrm in great location just 2 blocks to the Beach. 5 minute walk to many shopping & dining options. Easy access on & off the island. Heated pool. Sleeps 4

Spacious 2 bedroom, 3rd floor condo at The Anchorage with private deeded beach access to Crescent Beach. Great location, walk to shopping & restaurants. New furnishings, many amenities. Sleeps 6

Annual Rentals

Unfurnished 3 Bedroom, 3 bath private villa with new paint throughout, new carpet in bedrooms, new flooring in living room, new AC. Florida Room overlooks a lush tree lined greenbelt walking path, separating your home from the other Villas.

Charming & bright two bedroom, one bath condo located in the recently renovated Bay Oaks complex on Siesta Key. This is a furnished, turn-key unit with linens and a fully stocked kitchen (dishes, pots & pans, etc.) provided. Located on the ground flo


6623 Midnight Pass Road Siesta Key, FL 34242


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